Welcome to 101 Charlton Road, a charming 4-bedroom, 2.5-bath Cape Cod situated on a desirable corner lot. This well-maintained home features a main-level primary suite and beautiful hardwood floors throughout the main living areas. The spacious kitchen is equipped with stainless steel appliances, a center island, breakfast nook, and flows seamlessly into the separate dining room and inviting living room, perfect for everyday living and entertaining. Upstairs, you'll find three additional bedrooms, 1.5 baths, and the convenience of an upper-level laundry room. Enjoy outdoor living in the fenced backyard complete with a storage shed, rear deck, and plenty of space for pets, gardening, or gatherings. Relax on the welcoming covered front porch and enjoy the convenience of being just minutes from Historic Old Town Winchester, Shenandoah University, Winchester Medical Center, shopping, dining, local wineries, parks, and easy access to Routes 7, 50, and I-81 for commuting. All sizes are approximate. More photos coming soon
For sale
$429,900
101 Charlton Rd, Winchester, VA 22602
4beds
1,714sqft
Single Family Residence
Built in 1998
-- sqft lot
$364,600 Zestimate®
$251/sqft
$16/mo HOA
What's special
Fenced backyardDesirable corner lotMain-level primary suiteStorage shedSeparate dining roomWelcoming covered front porchCenter island
- 7 hours |
- 191 |
- 11 |
Zillow last checked:
Listing updated:
Listed by:
RoxAnn Grimes 540-327-2798,
RE/MAX Roots,
Listing Team: Roxann Grimes Team
Source: Bright MLS,MLS#: VAFV2042768
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
- Main level bathrooms: 1
- Main level bedrooms: 1
Basement
- Area: 0
Heating
- Forced Air, Natural Gas
Cooling
- Central Air, Electric
Appliances
- Included: Microwave, Dishwasher, Disposal, Dryer, Refrigerator, Stainless Steel Appliance(s), Cooktop, Washer, Electric Water Heater
- Laundry: Hookup
Features
- Breakfast Area, Ceiling Fan(s), Entry Level Bedroom, Floor Plan - Traditional, Eat-in Kitchen, Primary Bath(s), Upgraded Countertops
- Flooring: Carpet, Hardwood, Luxury Vinyl, Wood
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 1,714
- Total interior livable area: 1,714 sqft
- Finished area above ground: 1,714
- Finished area below ground: 0
Video & virtual tour
Property
Parking
- Parking features: Driveway
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Patio & porch: Deck, Porch
- Pool features: None
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 55I14267
- Zoning: RP
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Crawl Space
Condition
- New construction: No
- Year built: 1998
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Subdivision: Carlisle Heights
HOA
- Has HOA: Yes
- HOA fee: $190 annually
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $251/sqft
- Tax assessed value: $332,660
- Annual tax amount: $1,597
- Date on market: 6/22/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Estimated market value
$364,600
$346,000 - $383,000
$2,107/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/22/2026 | Listed for sale | $429,900+77.3%$251/sqft |
Source:  Bright MLS #VAFV2042768 Report a problem | ||
| 9/13/2019 | Sold | $242,500-1.8%$141/sqft |
Source: Agent Provided Report a problem | ||
| 7/31/2019 | Listed for sale | $247,000+9.8%$144/sqft |
Source: Bright MLS #VAFV152044 Report a problem | ||
| 9/23/2013 | Sold | $225,000+4.7%$131/sqft |
Source: Public Record Report a problem | ||
| 8/13/2013 | Pending sale | $214,900$125/sqft |
Source: Experience Realty Group LLC #FV8120635 Report a problem | ||
| 8/1/2013 | Price change | $214,900-2.3%$125/sqft |
Source: Experience Realty Group LLC #FV8120635 Report a problem | ||
| 6/29/2013 | Listed for sale | $219,900+2.5%$128/sqft |
Source: Experience Realty Group LLC #FV8120635 Report a problem | ||
| 4/17/2009 | Sold | $214,600+26.3%$125/sqft |
Source: Public Record Report a problem | ||
| 5/1/2003 | Sold | $169,900$99/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $1,597 +14.1% | $332,660 +21.2% |
| 2024 | $1,399 | $274,400 |
| 2023 | $1,399 +106% | $274,400 +23.2% |
| 2022 | $679 | $222,700 |
| 2021 | $679 -47.1% | $222,700 +5.8% |
| 2020 | $1,284 -50% | $210,500 |
| 2019 | $2,568 +116% | $210,500 +8% |
| 2018 | $1,189 +1.7% | $194,900 |
| 2017 | $1,169 +11.5% | $194,900 +11.5% |
| 2016 | $1,049 +7.1% | $174,800 |
| 2015 | $979 +103.4% | $174,800 +7% |
| 2014 | $481 | $163,300 |
| 2013 | -- | $163,300 -0.7% |
| 2012 | -- | $164,500 |
| 2011 | -- | $164,500 -18.5% |
| 2010 | -- | $201,800 |
| 2009 | -- | $201,800 -6% |
| 2008 | -- | $214,600 |
| 2007 | -- | $214,600 |
| 2006 | -- | $214,600 |
| 2005 | -- | $214,600 +63.7% |
| 2003 | -- | $131,100 |
| 2002 | -- | $131,100 |
| 2001 | -- | $131,100 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 22602
Nearby schools
GreatSchools rating
- 4/10Greenwood Mill Elementary SchoolGrades: PK-5Distance: 0.2 mi
- 5/10Admiral Richard E. Byrd Middle SchoolGrades: 6-8Distance: 4 mi
- 4/10Millbrook High SchoolGrades: 9-12Distance: 1.5 mi
Schools provided by the listing agent
- District: Frederick County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Virginia
- Frederick County
- Winchester
- 22602
- 101 Charlton Rd
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